Triethylamine → 4-(4'methoxyphenyl)-benzenesulfonyl-S-trityl-L-cysteine amide

HRID 352401Notes

Reaction equation

HRID 352401 reaction equation
[C:1]([S:20][CH2:21][C@@H:22]([C:24]([NH2:26])=[O:25])[NH2:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:34][O:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][C:45]([S:48](Cl)(=[O:50])=[O:49])=[CH:44][CH:43]=2)=[CH:38][CH:37]=1>C(Cl)Cl>[CH3:34][O:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]2[CH:47]=[CH:46][C:45]([S:48]([NH:23][C@H:22]([C:24]([NH2:26])=[O:25])[CH2:21][S:20][C:1]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)(=[O:50])=[O:49])=[CH:44][CH:43]=2)=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27947504'-Methoxybiphenyl-4-sulfonyl chlorideHCID 44432703(2R)-2-amino-3-((triphenylmethyl)sulfanyl)propanamide

Product 1

HCID 1317244584-(4'methoxyphenyl)-benzenesulfonyl-S-trityl-L-cysteine amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part C: To a solution of 2.93 grams (8.1 mmol) of S-trityl-L-cysteine amide in 50 mL of dry methylene chloride was added 2 equivalents of triethylamine followed by 2.29 grams (8.1 mmol) of 4-(4′-methoxyphenyl)phenylsulfonyl chloride. The solution was stirred at room temperature for one hour, then concentrated on a rotory evaporator. The resulting slurry was partitioned between ethyl acetate and water. The organics were washed with 5% potassium hydrogen sulfate, saturated sodium bicarbonate, and brine, dried over sodium sulfate, filtered and concentrated to give 4.2 grams of crude product. The crude material was purified by silica gel chromatography using 1:1 ethyl acetate:hexane as the eluent to yield 3.36 grams of pure N-(4-(4′methoxyphenyl)-benzenesulfonyl-S-trityl-L-cysteine amide as a white solid.

Workup

  1. concentrationconcentrated on a rotory evaporator
  2. customThe resulting slurry was partitioned between ethyl acetate and water
  3. washThe organics were washed with 5% potassium hydrogen sulfate, saturated sodium bicarbonate, and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give 4.2 grams of crude product
  8. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8bf0c0ec5cae4a4eafeb2c9833d6f2bf
Source dataset
uspto-grants-2004_06
Patent number
US06747027B1

Reaction notes

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